EP1714988A1 - Liant à haute resistance à partir de fines particules de polymères vinyllactam pour comprimés, sa production et son utilisation - Google Patents

Liant à haute resistance à partir de fines particules de polymères vinyllactam pour comprimés, sa production et son utilisation Download PDF

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Publication number
EP1714988A1
EP1714988A1 EP06112175A EP06112175A EP1714988A1 EP 1714988 A1 EP1714988 A1 EP 1714988A1 EP 06112175 A EP06112175 A EP 06112175A EP 06112175 A EP06112175 A EP 06112175A EP 1714988 A1 EP1714988 A1 EP 1714988A1
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EP
European Patent Office
Prior art keywords
binder
binders
weight
vinyl
mpa
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EP06112175A
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German (de)
English (en)
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EP1714988B1 (fr
Inventor
Karl Kolter
Hermann Ascherl
Bernhard Fussnegger
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BASF SE
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BASF SE
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C08F226/10—N-Vinyl-pyrrolidone
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen

Definitions

  • the present invention relates to binders based on finely divided, pulverulent vinyl lactam polymers, wherein the binders have an average particle size of up to 35 ⁇ m and a bulk density of up to 0.2 g / ml. Binders in the form of hollow-spherical bodies or parts of such hollow-spherical bodies with a wall thickness ⁇ 3 ⁇ m are preferred, the ratio of the diameter to the wall thickness being> 10. Furthermore, the invention relates to a method for producing such binder particles and their use for the production of tablets with high strength.
  • Binders are generally used in the production of compressed administration forms in order to improve the mechanical properties, in particular the breaking strength and the friability.
  • wet granulation and direct tabletting.
  • the binders can also be divided into wet binders and dry binders.
  • dry binders the application is as the name says in dry form, that is, there is no dissolution in a solvent.
  • Direct tableting is, of course, the more cost effective process because the individual components need only be mixed, but often the developments fail because there is no effective dry binder available.
  • the dry binder effect also plays a major role in roll compaction, since in this case too, a strong cohesion between the particles of the tablet constituents has to be produced. If this is not the case, a mechanically unstable Walzenkompaktat, which breaks down again in the comminution almost in the starting grain size, flows poorly and in the subsequent tableting does not provide sufficient resistance to fracture and friability.
  • binders are, for example, vinyl lactam polymers.
  • Vinyl lactam polymers are commercially available and are sold, for example, under the names Kollidon® (BASF Aktiengesellschaft) and Plasdone® (International Specialty Products Inc.).
  • the average particle size of these products is in the range of 50 to 250 microns.
  • the particles are thick-walled or of irregular structure and have higher bulk densities (cf. V. Bühler in "Polyvinypyrrolidone Excipients for Pharmaceuticals", pp. 18-20 and 186-188, Springer-Verlag Berlin Heidelberg, 2005 ).
  • EP-A 1 437 375 are known powdery vinylpyrrolidone polymers with high bulk density, which are obtained by spraying using a rotating disk.
  • the object of the present invention was to find binders based on polyvinyllactams with improved binder properties for the preparation of very solid tablets.
  • binders were found based on finely divided powdered vinyl lactam polymers having average particle sizes of 1 to 35 .mu.m.
  • these binders are in the form of hollow-spherical bodies or parts of such hollow-spherical bodies, the wall thickness of the hollow-spherical bodies being less than 3 ⁇ m and the ratio of the diameter of the hollow-spherical bodies to wall thickness being greater than 10: 1.
  • the D (4,3) value is used using the method of light diffraction.
  • This particle size should be less than 35 .mu.m, preferably less than 30 .mu.m and more preferably less than 20 microns, with a lower limit of the average particle size of 2 microns.
  • the wall thickness of the hollow-spherical body or the parts or fragments of such body should preferably be less than 3.0 microns, especially less than 2.5 microns and more preferably less than 2.0 microns, with a lower limit of 0.05 microns, and the ratio of the hollow sphere diameter to shell thickness should be greater than 10: 1 preferably greater than 12: 1, and more preferably greater than 15: 1.
  • the bulk density is generally less than 0.2 g / ml, in particular 0.05 to 0.18 g / ml. Bulk density is determined according to Pharm. Eur. 2.9.15.
  • the BET surface area is usually above 1 m 2 per gram and can be up to 50 m 2 / g.
  • polyvinyllactams are water-soluble homopolymers, copolymers, terpolymers, block copolymers or graft copolymers. These polymers may contain as the following lactam-type monomers N-vinylpyrrolidone or N-vinylcaprolactam or mixtures thereof.
  • Suitable further comonomers are the Vinylester of the saturated C 1 - C 20 carboxylic acids such as vinyl acetate, vinyl propionate, vinyl laurate, vinyl stearate.
  • water-soluble copolymers of vinylpyrrolidone and vinyl acetate and very particularly preferably ratios of vinylpyrrolidone to vinyl acetate of 60:40 to 80:20, in particular copolymers of N-vinylpyrrolidone and vinyl acetate in a weight ratio of 6: 4, K value 25-30.
  • Homopolymers of N-vinylpyrrolidone are also preferred.
  • the K values according to Fikentscher a measure of the molecular weight of the polymers, can be from 10 to 120, preferably from 12 to 90, particularly preferably from 15 to 60.
  • binders which consist of 100% by weight of polyvinyllactam polymers.
  • additional substances may be added.
  • plasticizing substances can be added to improve the plasticity of the binder.
  • plasticizing agents typical plasticizers such as triethyl citrate, triacetin, propylene glycol, glycerol, polyethylene glycol and similar known substances can be used.
  • the proportion of these substances in the binder according to the invention is 0 to 20 wt .-%, preferably less than 10 wt .-%.
  • the binders according to the invention may also contain surface-active substances in addition to the vinyllactam polymer.
  • Surface-active substances are substances that bind to reduce the interfacial tension of an interface.
  • Suitable surfactants are, for example, salts of fatty acids such as sodium dodecylate, sodium stearate, sodium oleate or sodium palmitate and salts of alkyl sulfates such as sodium lauryl sulfate.
  • Suitable surfactants are, for example, salts of fatty acids such as sodium dodecylate, sodium stearate, sodium oleate or sodium palmitate and salts of alkyl sulfates such as sodium lauryl sulfate.
  • polyoxyethylated sorbitan fatty acid esters such as polysorbate 20 or ethoxylated 12-hydroxystearic acid or polyglycerol fatty acid esters.
  • ethoxylated derivatives of castor oil or hydrogenated castor oil for example reaction products of 35 mol of ethylene oxide with castor oil or of 40 mol of ethylene oxide with hydrogenated castor oil.
  • Such surfactants can be used in amounts of 0 to 20 wt .-%, preferably up to 10 wt .-%.
  • spray-drying processes are suitable in which a solution of the vinyl lactam polymers is finely atomized with the aid of nozzles and then dried in a stream of warm air.
  • aqueous solutions are processed.
  • one-fluid nozzles or multi-fluid nozzles can be used.
  • a multi-fluid nozzles are in particular two-fluid nozzles into consideration. It is crucial that the small droplets are achieved and the dried particles do not stick together.
  • the atomization takes place at high pressure for the respective nozzle type.
  • nozzle diameters of from 0.1 to 3 mm, preferably from 0.2 to 1 mm, particularly preferably from 0.4 to 0.8 mm, and pressures above 8 MPa have proven particularly useful, preferably greater than 12 MPa, very particularly preferably greater than 16 MPa.
  • the atomization pressure may be up to 25 MPa in the case of the single-fluid nozzle.
  • nozzle diameters are from 0.6 to 10 mm, preferably 0.8 to 3 mm, more preferably 1 to 3 mm and pressures of the atomizing gas are above 0.2 MPa, more preferably above 0.4 MPa , most preferably over 0.6 MPa proven.
  • the pressure of the atomizing gas can be up to 1 MPa.
  • Suitable atomizing gases are the same gases as used for drying.
  • the solids concentrations of the solutions to be sprayed are between 1 and 35 wt .-%, preferably between 3 and 25 wt .-% and particularly preferably between 5 and 15 wt .-%.
  • the atomization can be done in any spray tower conventional design.
  • drying gases air or inert gases such as nitrogen, argon or helium can be used, which can be passed through the drying tower in cocurrent or in countercurrent to the liquid droplets.
  • the drying gas is used in direct current.
  • the tower inlet temperature of the drying gas is 80 to 250, preferably 100 to 200 ° C.
  • the tower exit temperature is 40 to 130, preferably 50 to 110 ° C.
  • the evaporation of the solvent can be carried out both at atmospheric pressure and at slight over or under pressure (+/- 0.01 MPa).
  • the resulting powder can be separated from the gas stream, for example via a cyclone or a filter.
  • products sprayed in this way can be mixed with the customary mills such as, for As air jet mills, pin mills are ground.
  • the average particle size can be adjusted, for example, to values of 1 to 20 ⁇ m.
  • the application of the products according to the invention is usually carried out by mixing with the other formulation ingredients and then compressing to form a tablet or a compact. It is crucial that the dry binder is evenly distributed in the mixture. According to a particular embodiment, even after mixing water, steam or an organic solvent may be added, whereby the small particles dissolve and lead to a strong strength of the tablet or Kompaktats.
  • the preparation of a tablet is usually carried out on a tablet press, the production of a Kompaktats on a Walzenkompaktor.
  • the compact is comminuted again to a granulate that can be mixed with other additives and z. B. can be pressed into a tablet.
  • the process of roll compaction is also referred to as dry granulation.
  • Compression into tablets can be carried out at pressures of up to 800 MPa.
  • the tablets obtained with the aid of the binders according to the invention have a high strength.
  • the strength can be from 40 to 600 N.
  • the proportion of the dry binder in the formulation should be 0.5 to 20% by weight, preferably 1 to 15% by weight and more preferably 2 to 12% by weight. Because the dry binders according to the invention have enormous binding properties, it is also possible to compress poorly compressible active ingredients and auxiliaries, especially if they are also present in high concentrations.
  • binders of the present invention even due to the fine particles, have poorer flowability. So should also result in the mixture with other ingredients a poorer flowability. Surprisingly, however, better flowabilities result in these cases.
  • binders are sticky substances that increase the ejection forces of tableting, which can cause numerous problems, such as: B. reduced strength of the tablet, covers, strong heating of the pressing tools and the die wall, increased wear of the press, etc.
  • the binders of the invention show a lubricant effect, because the residual and ejection forces during tabletting are significantly lower than without the use of a binder or with Use of a conventional binder.
  • the binders of the invention lead to tablets with exceptional mechanical properties, they allow the compression of non-or difficult-to-compress drugs, they allow a reduction of the total tablet mass or the tablet volume and they ensure a smooth course of Tablettierreaes.
  • the spray dryer used was a pilot-scale spray tower from Niro, type Minor (Examples 1, 3-8, 12, 13) or a Zimmerling production spray tower, diameter 7 m (Example 2).
  • the spray solution was heated to 80 ° C before sputtering, and atomization into fine droplets was carried out by means of a single-fluid nozzle (diameter 0.5 mm) at 16 MPa pressure.
  • the exhaust air temperature was 85 ° C.
  • the spray solution was heated to 80 ° C before sputtering, and atomization into fine droplets was carried out by means of a single-fluid nozzle (1.2 mm diameter) at 18 MPa pressure.
  • the exhaust air temperature was 72 ° C.
  • the microscopic examination showed the presence of hollow spheres and fragments of hollow spheres (shells) with wall thicknesses of 1.0 ⁇ m.
  • a solution of 10% Kollidon 30 (polyvinylpyrrolidone, K value 30) and 0.3% triethyl citrate in water was prepared and dried in a spray dryer at a supply air temperature of 145 ° C.
  • the spray solution was heated to 75 ° C before sputtering and sputtering into fine droplets was carried out by means of a single-fluid nozzle (diameter 0.5 mm) at 16 MPa pressure.
  • the exhaust air temperature was 71 ° C.
  • a fine powder having an average particle size of 16 ⁇ m and a bulk density of 0.11 g / ml was obtained.
  • the microscopic examination showed the presence of hollow spheres and Bruck pieces of hollow spheres (shells) with wall thicknesses of 1.2 microns.
  • a solution of 10% Kollidon 30 and 0.5% polysorbate 80 in water was prepared and dried in a spray dryer at a feed air temperature of 145 ° C.
  • the spray solution was heated to 75 ° C before sputtering, and the sputtering into fine droplets was carried out by means of a single-fluid nozzle (diameter 0.4 mm) at 16 MPa pressure.
  • the exhaust air temperature was 71 ° C.
  • a fine powder with a mean particle size of 13 ⁇ m and a bulk density of 0.11 g / ml was obtained.
  • the microscopic examination showed the presence of hollow spheres and Bruck pieces of hollow spheres (shells) with wall thicknesses of 0.9 microns.
  • a solution of 5% Kollidon VA 64 and 0.1% sodium lauryl sulfate in water was prepared and dried in a spray dryer at a supply air temperature of 165 ° C.
  • the spray solution was heated to 78 ° C before sputtering and sputtering into fine droplets was carried out by means of a single-fluid nozzle (diameter 0.4 mm) at 20 MPa pressure.
  • the exhaust air temperature was 79 ° C.
  • a fine powder having an average particle size of 13 ⁇ m and a bulk density of 0.09 g / ml was obtained.
  • the microscopic examination showed the presence of hollow spheres and Bruck pieces of hollow spheres (shells) with wall thicknesses of 0.8 microns.
  • a 10% aqueous solution of a copolymer of N-vinylpyrrolidone and N-vinylcaprolactam in the weight ratio 1: 1 (K value 65, measured 1 wt .-% in water) was dried in a spray dryer at a supply air temperature of 170 ° C.
  • the spray solution was heated to 80 ° C before sputtering and sputtering into fine droplets was carried out by means of a single-fluid nozzle (diameter 0.4 mm) at 18.5 MPa pressure.
  • the exhaust air temperature was 83 ° C.
  • a fine powder having a mean grain size of 19 ⁇ m and a bulk density of 0.12 g / ml was obtained.
  • a 12 wt .-% aqueous solution of a copolymer of vinyl pyrrolidone and vinyl laurate (average molecular weight 20,000 daltons, K value 19) in a weight ratio of 90:10 was dried in a spray dryer at a supply air temperature of 160 ° C.
  • the spray solution was heated to 90 ° C before sputtering, and the atomization into fine droplets was carried out by means of a single-fluid nozzle (diameter 0.5 mm) at 16 MPa pressure.
  • the exhaust air temperature was 77 ° C.
  • a fine powder having an average particle size of 16 ⁇ m and a bulk density of 0.11 g / ml was obtained.
  • a solution of 10% Kollidon VA 64 and 0.25% Cremophor RH 40 (reaction product of hydrogenated castor oil with 45 moles of ethylene oxide) in water was prepared and dried in a spray dryer at a supply air temperature of 165 ° C.
  • the spray solution was heated to 78 ° C before sputtering and sputtering into fine droplets was carried out by means of a single-fluid nozzle (diameter 0.4 mm) at 20 MPa pressure.
  • the exhaust air temperature was 79 ° C.
  • the microscopic examination showed the presence of hollow spheres and fragments of hollow spheres (shells) with a wall thickness of 1.0 ⁇ m.
  • Kollidon VA 64 commercial product BASF, average particle size 57 ⁇ m binder Breaking strength (N) Friability (%) Decay (min.)
  • Example 5 92 ⁇ 0.1 9 Kollidon 64 merchandise 63 0.4 13
  • the microscopic examination showed the presence of hollow spheres and Bruck pieces of hollow spheres (shells) with wall thicknesses of 1.1 microns.
  • a 30% aqueous solution of Kollidon VA 64 was dried in a spray dryer at a supply air temperature of 153 ° C.
  • the spray solution was heated to 87 ° C before atomization and the atomization into fine droplets by means of two-fluid nozzles (diameter: liquid supply 2 mm, gas side annular gap 1 mm) at 0.6 MPa gas pressure.
  • the exhaust air temperature was 83 ° C.
  • a fine powder having a mean grain size of 15 ⁇ m and a bulk density of 0.12 g / ml was obtained.
  • the microscopic examination showed the presence of hollow spheres and Bruck pieces of hollow spheres (shells) with wall thicknesses of 1.5 microns.

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  • Medicinal Chemistry (AREA)
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  • Pharmacology & Pharmacy (AREA)
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EP06112175A 2005-04-20 2006-04-03 Liant à haute resistance à partir de fines particules de polymères vinyllactam pour comprimés, sa production et son utilisation Expired - Lifetime EP1714988B1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102005018465A DE102005018465A1 (de) 2005-04-20 2005-04-20 Bindemittel für Tabletten mit hoher Festigkeit auf Basis von Herstellung und Verwendung von feinteiligen Vinyllactampolymerenn, deren Herstellung und Verwendung

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EP1714988A1 true EP1714988A1 (fr) 2006-10-25
EP1714988B1 EP1714988B1 (fr) 2008-01-09

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EP06112175A Expired - Lifetime EP1714988B1 (fr) 2005-04-20 2006-04-03 Liant à haute resistance à partir de fines particules de polymères vinyllactam pour comprimés, sa production et son utilisation

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US (1) US8268350B2 (fr)
EP (1) EP1714988B1 (fr)
JP (1) JP4327818B2 (fr)
CN (1) CN1854232B (fr)
AT (1) ATE383381T1 (fr)
DE (2) DE102005018465A1 (fr)
ES (1) ES2299142T3 (fr)

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Publication number Priority date Publication date Assignee Title
DE102005049001A1 (de) * 2005-10-11 2007-04-12 Basf Ag Verfahren zur Herstellung von direkttablettierbaren Ibuprofen-Formulierungen
EP2046854B1 (fr) * 2006-07-21 2019-12-04 Basf Se Mousses de polyuréthanne à effet désinfectant et/ou blanchissant

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0687694A2 (fr) * 1994-06-17 1995-12-20 Basf Aktiengesellschaft Procédé pour la préparation de polymères à base de 1-vinylimidazoles
EP0715848A2 (fr) * 1994-12-06 1996-06-12 BASF Aktiengesellschaft DépÔt médicamenteux contenant de l'alginate et un agent liant polymériques
EP1437375A1 (fr) * 2003-01-08 2004-07-14 Dai-Ichi Kogyo Seiyaku Co., Ltd. Procédé de fabrication d'une poudre de polyvinylpyrrolidone

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US5176713A (en) * 1987-07-15 1993-01-05 Colgate-Palmolive Co. Stable non-aqueous cleaning composition method of use
US4986048A (en) 1990-01-11 1991-01-22 Pittsburgh Corning Corporation Method and apparatus for erecting a glass block wall
US4968562A (en) * 1990-02-27 1990-11-06 Minnesota Mining And Manufacturing Company Hollow acid-free acrylate polymeric microspheres having multiple small voids
DE4139963A1 (de) 1991-12-04 1993-06-09 Basf Ag, 6700 Ludwigshafen, De Redispergierbares dispersionspulver aus n-vinylpyrrolidon-vinylacetat-copolymerisat, dessen herstellung und verwendung
US5252704A (en) * 1992-06-05 1993-10-12 Air Products And Chemicals, Inc. Redispersible polymer powders using polyvinyl pyrrolidone as a dispersing aid
DE4442900A1 (de) 1994-12-02 1996-06-05 Basf Ag Verfahren zur Herstellung von pulverförmigen Wasserstoffperoxid-Polymer-Komplexen
US8236352B2 (en) * 1998-10-01 2012-08-07 Alkermes Pharma Ireland Limited Glipizide compositions
US6969529B2 (en) * 2000-09-21 2005-11-29 Elan Pharma International Ltd. Nanoparticulate compositions comprising copolymers of vinyl pyrrolidone and vinyl acetate as surface stabilizers
DE19915420A1 (de) * 1999-04-06 2000-10-12 Basf Ag Stabilisierte Polyvinylpyrrolidon-Zubereitungen
CN1226320C (zh) * 2003-06-30 2005-11-09 厦门大学 N－乙烯基吡咯烷酮和乙酸乙烯酯共聚物的制备方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0687694A2 (fr) * 1994-06-17 1995-12-20 Basf Aktiengesellschaft Procédé pour la préparation de polymères à base de 1-vinylimidazoles
EP0715848A2 (fr) * 1994-12-06 1996-06-12 BASF Aktiengesellschaft DépÔt médicamenteux contenant de l'alginate et un agent liant polymériques
EP1437375A1 (fr) * 2003-01-08 2004-07-14 Dai-Ichi Kogyo Seiyaku Co., Ltd. Procédé de fabrication d'une poudre de polyvinylpyrrolidone

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ATE383381T1 (de) 2008-01-15
JP4327818B2 (ja) 2009-09-09
ES2299142T3 (es) 2008-05-16
EP1714988B1 (fr) 2008-01-09
CN1854232B (zh) 2010-10-13
DE102005018465A1 (de) 2006-11-02
DE502006000273D1 (de) 2008-02-21
US20060240102A1 (en) 2006-10-26
CN1854232A (zh) 2006-11-01
US8268350B2 (en) 2012-09-18
JP2006316266A (ja) 2006-11-24

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